Caulker has been called up to the England squad by Roy Hodgson for their friendly with Denmark next week and now has a good chance of making the plane to Brazil in the summer.
The centre back has been in fine form as Cardiff captain this season since his permanent switch from Spurs in the summer, but Sherwood has admitted that he would not have sold him.
The new Tottenham gaffer knows Caulker very well from his time in the club’s development squad and claims he would have guaranteed him more first team football if he were in charge.
“He wanted game time and more than the previous manager would guarantee him,” said Sherwood.
“The club decided they would let the player go and they think they had a good deal. It is up to Steven to build on that and prove the club were wrong to let him go.
“He wanted to go and play. The only thing I could have done is say ‘you will play more football’.”
Caulker will line up against Spurs today for the first time.